The Summer at Lake Valor
by Platinum Daylight
Summary: When Top Coordinator Dawn Berlitz finally gets chance to meet her penpal Drew Hayden, she decides to use this as an opportunity to reunite him with his old flame, May. But little do they know, everything is about to change when the lives of Dawn, May, Misty, Gary, Drew, and Ash collide at Lake Valor's Hotel Grand Resort. Major Pokeshipping, Contestshipping, and Cavaliershipping.
1. Chapter 1

_RoseradePetals has just logged on!_ Dawn was in earshot of the ping noise her laptop made from receiving the notification. That was probably Andrew, her internet pen pal from Hoenn. They'd been exchanging messages through the _**pokepen**_ chatrooms for the past several months. Pokepen was _**nothing**_ like your average social media site, full of demanding creeps who harass others. Pen pals were assigned here, paired up by interests and trainer description. Andrew was a Coordinator, just like Dawn. And she was determined to meet him today at the Lakeside Resort's Grand Hotel at Lake Valor for the summer trip.

 _NoNeedToWorry has just logged on!_ Dawn slid into her seat and clicked on Andrew's chat box, opening up the new message he sent her.

 **RoseradePetals:** _I imagine that username of yours only makes people worry more. LOL!_

 **NoNeedToWorry:** _Oh, give me a break "Roserade Petals" what were you even thinking?_

 **RoseradePetals:** _Hey, Roserade is a very elegant Pokemon! You wouldn't be knocking my username if you knew a thing or two about that. :P_

 **NoNeedToWorry:** _All of your usernames always have something to do with roses, makes me wonder if you're even a guy. Probably a catfish. :o_

 **RoseradePetals:** _Well you're about to find out today, aren't you? Who knows, you're probably the catfish, Dawn! How do I know you're not like, Team Rocket or something behind those emails? Probably reeling me in so you can force me to join you!_

 **NoNeedToWorry:** _UM! Morbid much? That was like the worst thing you could come up with lmao but Arceus, never! Anyways, don't worry, you're going to meet two coordinators today because my BFF May is going to be there right next to me._

 **RoseradePetals:** _Whoa, wtf that's crazy you know, cause' I dated a Coordinator named May at one point lmao_

 **NoNeedToWorry:** _"Dated" as in past tense, because you probably scared her off with your obsession with Roserade petals._

 **RoseradePetals:** _Let's see if you'll be so cheeky when we meet IRL!_

 **NoNeedToWorry:** _Same to you! But_ _you know I don't mean that._

 **RoseradePetals:** _Better. She... truly meant a lot to me. It's a long story._

 **NoNeedToWorry:** _Maybe you could tell me at the Lakeside Resort if you feel like it._

 _RoseradePetals is typing…_

"Dawn!" A voice called from outside, followed up with a sound of a car honking. That was May, waiting for her to come outside. Her little red car was visible from the corner of the window.

 _Shoot,_ Dawn sped over to her window and opened it, "Hold on, May. I'll be right there!" she quickly popped back down her chair to say goodbye to Andrew.

 **NoNeedToWorry:** _Anyways, I gtg. Ttyl.. irl_ _I'm actually really looking forward to it!_

 **RoseradePetals:** _Yeah, same here. See you!_

 _No_ _NeedToWorry_ _has logged off._

 _RoseradePetals has logged off._

"Coming!" Dawn yelled out, shutting off her laptop and packing it inside her suitcase. She ran downstairs and made her way out. Johanna kissed her goodbye and saw her off as she rushed into May's car.

"God, Dawn. What was holding you up?" May put her foot on the pedal and turned right out of Dawn's house, checking her mirrors. "Was it that pen pal of yours again? Andrew?"

"Yeah, sorry about that." Dawn strapped on her seatbelt slumping into her seat, "We were just talking and we're finally going to meet at the Lakeside Resort! I get to spend the whole summer hanging out with you _**and**_ my pen pal in person! How great is that?" For Dawn, this was going to be a great experience. Only the most accomplished Pokémon Trainers were invited out to this year's summer trip. Both Dawn and May had become grand festival champions at some point over the years, which qualified invitations for each of them. That meant Andrew had to have been a pretty good Coordinator himself.

But May, however, was not all that enthusiastic. She was silent, uncomfortable. When the traffic light turns red, her eyes were staring straight at the road, contemplating something. She and Dawn had kept a pretty solid friendship over the years. They even began travelling together right after they both won a grand festival contest from their respective regions. But the last several months hadn't exactly been so easy for May, not since Dawn had signed up for a pen pal service over the internet. She was never against her communication with Andrew. It's just that the more Dawn talked about him, the more he sounded like-

"Um… May?"

May shook her head, snapping from her daze, "You're fine, Dawn. It's just—your pen pal somehow reminds me an awful lot of my first true love." Her heart tightened up at the confession.

Dawn raised her eyebrows in surprise, "What?! No way! Oh, come on, May. Now you've gotta tell me everything."

"Okay, I used to date this Coordinator I was traveling with before I competed at the Grand Festival in Hoenn again, and I know that has absolutely nothing to do with your pen pal but when you told me he was a Coordinator from the Hoenn region, that was the first person I thought of. Those letters Andrew sent you reminded me of everything I used to share with him." May said this all in one breath, trying not to reel from her memories because she was on the road.

"I'm so sorry, May. I had no idea." Dawn's voice took on a soft but shocked tone. She supposed this was just one of the few things she didn't know about her. But with the disappointment layering over May's face, Dawn couldn't blame her for not talking about it. But then she suddenly remembers the message Andrew sent her. _That's crazy you know, cause' I dated a Coordinator named May at one point._ May didn't know that Andrew told her that, though. "I don't mean to pry, but could you tell me his name? Are you two still in contact?" Dawn asked, her eyes filled with curiosity.

She paused, trailing off, brown bangs falling over the corner of her eye, "His name was Drew. And I never saw him ever again."

The moment the light turns green again is exactly when Dawn put two and two together. An _ **drew,**_ the name clicks into her brain, with emphasize on Drew. Dawn didn't think much of it then, but now she knew just exactly who she'd be looking for.

* * *

The Lakeside Resort is bustling with crowds of elite trainers and top coordinators. Most of them were recognizable because of the fame they'd obtained. When the both of them arrived, their baggage's were picked up by a few bellboys to be moved to wherever their assigned suite was.

"I wonder if I'll see anyone I know." Dawn said, referring to old friends rather than celebrities she'd competed with in the past. She'd hope to be able to see what they were all up to after all these years. It was mostly all in the news.

Ash went back home to Pallet Town to start all over and won the Kanto League.

Brock achieved his dream of becoming a Pokémon Doctor, working alongside Nurse Joy.

Cupid Lyra managed to beat out Lance and became Johto's newest Champion… and opened a matchmaking business after that.

Kenny finally became a Top Coordinator.

Nando became a Top Coordinator _**and**_ made top four in multiple conferences.

Barry became a poketech model.

And Gary Oak was now one of the most renowned Pokémon Researchers to date.

Lastly, there was Zoey. She was still a traveling Top Coordinator, but Dawn never heard much from her after they competed against each other for the second time in the Sinnoh Grand Festival, which resulted in Dawn's first victory against her.

It was nice to know they'd all become so accomplished, but it wasn't quite the same as when Dawn was traveling with Ash and Brock.

"After that Veilstone City traffic I had to go through, I just hope I don't see some of my old rivals here." May puffed, crossing her arms. "Anyways, my suite number is 192. So, meet me there if you need me!" May waved, taking off.

"Alright!" Dawn waved back, waiting for May to be out of sight before initiating her plan. As Lyra used to say, for this matchmaker—it's cupid time!

* * *

"Could I get this note to go to Drew's room? You know, the Coordinator Drew? It's _**very**_ urgent." Dawn slipped a hundred-dollar bill to the receptionist with the note.

The receptionist nods, taking the cash and sending a bellboy to do the favor.

"Thank you so much!" Dawn winked, waving off, "You're a huge help!"

"Please don't tell me that was a love letter to the famous Top Coordinator Drew." A voice crept up on Dawn from behind.

"Oh, as if!" Dawn put her hands on her hips, her chin raised up, not facing the source of the sound. "I'll have you know, I'd never have feelings for someone I haven't even met! Let alone write a love letter."

"Well, that's good, because then I'd have to trash this poem I wrote for you if you had eyes for someone else."

"Huh?" Dawn's eyes perked up, that voice sounded familiar. Her blue locks whip around her shoulders when she turns around to face the source. "Gary?! You're here too?!"

Gary chuckled, his brown hair was messier than ever, "Surprise, haven't seen you in a while." His arms spread wide open.

"No kidding! Oh, my god, I missed you!" Dawn exclaimed, skipping over to give him a quick, tight hug. "Tell me how you've been! I haven't seen any of my old friends in forever, you know. C'mon, you've gotta tell me about the cool adventures and breakthroughs you've had as a researcher!"

"And I will, Dawn." Gary assured her, "But not before you tell me about _**your**_ journey leading up to your fame as a Top Coordinator. You've been in so many Grand Festivals!"

Dawn beamed at him, "Well, that's no fair because I asked first!"

"Okay, we'll play rock, paper scissors. Best two out of three! Loser has to go first." Gary pumped his fist.

"Oh, you are _**so**_ on!" Dawn pumped up her fist as well.

"Rock, paper, scissors…"

* * *

An envelope slipped in room number 190, Drew Hayden's suite. His eyes perked up in curiosity, picking it up and opening it.

 _Hey there, Andrew!_

 _Or should I say RoseradePetals?_

 _Today is finally the day, huh?_

 _Anyways, if you're reading this, it means we've both finally arrived._

 _So, I've got this great idea._

 _In thirty minutes, come meet me at Suite #192._

 _It'll save the trouble of looking for each other in this huge crowd._

 _\- NoNeedToWorry_

Drew chuckled. So, she's finally here. And only two doors down from him, too. He flipped his green bangs from his eyes, _Alright, Dawn. See you later._

* * *

"I cannot believe we're roommates!" May exclaimed excitedly, hugging Misty, "If I'd known you'd be here, I would've told Ash when he called me from the PC in the Pokémon Center!"

"Wait, Ash is going to be here too?!" Misty gasped, "I haven't seen him since he won the Kanto League, god he's becoming a greater trainer each and every day. It's like he turned into a full champion right before my eyes! May, he looked SO different when we reunited in Kanto. It was like the boy I once knew finally became a man!" she said that last bit in a dreamy tone.

May blinked, going through her thoughts, "Misty, are you and Ash..." she twiddled her thumbs, which has been a habit for her every time she asked a question that made her feel uncomfortable "…You know— "

There fire set in Misty's eyes were as red as her hair, "NO FREAKIN' WAY!" she yelled, tossing a nearby pillow at May, causing her to fall face down on the ground, "AS IF I'D EVER! NOT WITH THAT KID!"

"G-Guess it was wrong to step on that minefield…" May stammered, her body lying flat on the floor.

Before Misty could spit out anymore disgust with May, there was a knock on the door. A voice rang from the other side. "May, open up! It's me!"

"O-Oh look, right on time! Misty, you really need to meet my best friend Dawn, she was also one of Ash's traveling companions!" May rushed up off the ground and ran to the door, pulling Dawn in and shutting it quickly.

"Uh—" Dawn started, only to be cut off by May.

"Dawn, Misty. Misty, Dawn."

"Oh, my gosh!" Dawn clapped her hands together and beamed, "You're even cuter as a full sized human!"

"Um, what?" Misty uttered in confusion.

"Oh, when Ash and I journeyed together, we went fishing once. And he took out the CUTEST red-headed fishing lure and told me you gave it to him. He wouldn't even let me touch it!"

Misty nearly blushed, "H-He still kept it? After all that time?"

"Wow, Misty. He must have told Dawn _**all**_ about you." May smirked at her.

The faint red streak from Misty's face had vanished as soon as May said that, shooting a deathly glare at her "For the last time, May—"

" _ **Anyways**_ ," Dawn announced, shaking her head, "Listen up! I came here because my pen pal is going to be knocking on that door at any moment, we're finally going to meet him for the first time!" She directed that last bit to May, looking her in the eye.

"A pen pal? Misty tilted her head, letting the reality of what she said seep into her brain before scrunching her face in repulsion, "YOU MEAN SOME GROSS, CREEPY STRANGER ON THE INTERNET IS GOING TO KNOCK ON OUR SUITE?! DAWN, YOU'VE GOTTA GET RID OF HIM!"

But Misty would find that it was too late, as someone was already knocking on the door, "Oh, great…" Misty softly grumbled, rushing over the kitchen counter to hide while May followed suit.

"Shhh," Dawn whispered, placing a finger on her lip, "Quiet." She turned on the handle, revealing a mop of green hair on a male figure.

"Dawn?" his yes dilated upward.

"Mhm, An _ **drew**_." Dawn nodded, smirking.

"Well, what do you know." Drew flipped his bangs with his fingers, "My pen pal was _**the**_ Top Coordinator Dawn. And here I thought I was talking to a complete nobody." He laughed at his own joke.

Dawn beamed at him, "Trust me, today is going to be _**full**_ of surprises. Guess I was wrong about you being catfish, why don't you come in? I want you to meet May and Misty. She widened the door opened.

He took a few steps inside the suite, with Dawn following behind.

"Okay, guys, you can come on out and meet _**Drew**_." Dawn said with as much clarity in her voice possible.

"Wait, _**Drew?**_ " May's head was the first to pop up. She walked over to him in disbelief, "No way…"

Drew took a step back, the shock was slowly morphing its way into his face, "May?!"

Dawn stood by and watched the scene unfold as the two stared at each other in awe and surprise.

"Hey." May started.

"It's been awhile-" Drew beamed at her faintly.

Misty popped out from the kitchen counter angrily, "You invited a _**fuckboy**_ into our suite?! Dawn, I'm going to let this one slide since you probably didn't know any better, but he can't be trusted!"

Drew's eyebrows furrowed, "Okay, who's the redhead and what the hell's her problem?"

Misty quickly jumped in between May and Drew and got in his face, "LISTEN HERE, ROSE BOY. I'M THE GIRL WHO HAD TO LISTEN TO MAY CRY ABOUT YOUR SHITTY ASS REASON FOR BREAKING HER HEART. SO, I'M NOT ABOUT TO LET YOU PLAGUE DAWN'S LIFE AS WELL!"

"Misty, stop! It's okay!" May grabbed her by the arms, holding a thrashing Misty back from rearranging Drew's face.

"Whoa!" Dawn exclaimed, running over to help May, pulling Misty back from him as much as possible.

"HOW DARE YOU SHOW YOUR FACE HERE! YOU THINK JUST BECAUSE YOU GOT ALL YOUR FANCY RIBBONS AND TROPHIES NOW MEANS THAT YOU CAN WORM YOUR WAY BACK INTO HER LIFE?!" Misty swung her arms and legs over and over, "MAY, DAWN, LET GO OF ME. I'M ABOUT TO SHOW THIS NO-GOOD SNOT THAT HE CAN'T FLOWER POWER HIS WAY INTO EVERYTHING!"

Dawn tightened her grasp on Misty's arm, "Drew!" she grunted, "Step back!"

"Drewy-kins!" A familiar, feminine voice interrupted, the sound of heels clicked into the room, "Are you done meeting your pen pal yet? I got tired of waiting."

"Drewy-kins?" May grimaced, loosening her grip on Misty.

Dawn let go, whipping her head to the source of the voice. From the bottom of her Mary-jane heels to her signature pastel blue dress and strawberry blonde hair drills—it was Ursula.

"What's the prissy Barbie doing here?" Misty snorted as soon as she stopped her thrashing completely.

"Excuse me, _**Ariel**_ but my name's Ursula and I'm here because you and your little friends are holding my boyfriend hostage." She rolled her eyes, and shot Dawn a look, "Nice seeing you again, Dee Dee."

"Boyfriend?" May snapped her head towards Drew, who looked at her with as much disappointment.

 _Looks like my matchmaking plan was a bust._ "Why don't you come over here and say that to my face!" Dawn challenged her, stepping forward with her fist clenched, only for Misty to grab her wrists. Never in her life did she hate Kenny so damn much.

"It's not worth it, Dawn. The people in China would just make another one in her place." She smirked at the displeasure surfacing in Ursula's face.

"I just love it when exes downgrade." Misty's smirk doesn't falter.

"Oh, please!" Dawn exclaimed, "Drew is way too down to earth to go out with someone like _**you**_."

"Well then, I hate to break it to you _**Dee Dee**_ , because we've been an item ever since he started sending letters to that pen pal of his." Ursula nearly hissed, "So which one of you is it?"

"That would be me." Dawn said sweetly, watching the lines scrunch up on Ursula's forehead.

"Well, Drew. I think it's time for you to leave! You wouldn't want to catch dandruff in your perfect hair now, would you?" Ursula smirked.

Dawn took out Pachirisu's pokeball, "I'm about to show you how I got that nickname in the first place!"

"Dawn, stop." Drew finally said, "And you stop, too, Ursula." He shot a glare at her, "She's my friend and she's just as important to me as you are. So, can you guys please try to be civil? At least around me?" he pleaded.

Dawn was the first to give in to agreement, pocketing away Pachirisu's pokeball. "Okay, sure."

Ursula rolled her eyes, letting out a very exaggerated sigh before responding, "Fine, but you're coming back to my suite once you're done!"

Misty interjected, "Actually, he should just get going right about now. I mean, you do know that it's rude to leave your trash in other people's suites, right?"

" _ **Misty.**_ " May hissed, "That's enough. If Dawn and Ursula can agree to be civil with each other for Drew's sake, then you and Drew should do it for mine."

Misty looked at her guiltily, "I'm sorry, I was just trying to look out for you."

"Hey, I was civil." Drew pointed out, "She was the one that started it."

Misty shook out of her apologetic mood, cracking her knuckles together, "Why don't I go ahead and finish it then, huh?"

" _ **You guys!**_ " May yelled.

"Okay, sorry we'll be civil." Both Misty and Drew said in unison.

* * *

When all was said and done, Drew and Dawn made reservations at the Seven Star Restaurant to have lunch tomorrow. It was the end of the day, and Dawn hadn't even got a chance to see her suite yet.

"Alright, #191 is right next to May and Misty's suite." Dawn took out her key card, sliding it through the lock, "I wonder who my roommate is going to be…" she murmured to herself, walking inside the room. Her bags were placed near the living room couch, next to a few other different suitcases.

Maybe it'll be someone she knew, like Zoey. It would've been great for them to catch up again, it might even be a gym leader like Candice or Maylene. Dawn always got along with those two very well. Or, it could've be Lyra. That didn't sound too bad.

Dawn nearly dropped her jaw at the pastel drenched figure with stiff strawberry blonde hair curls. "Arceus, **_hell_** no."

 _Or, it was Ursula._

"Hell no is right." Ursula retorts, "What do you think **_you're_** doing here, **_Dee Dee_**?"

"What am I doing here?! This is my suite!" Dawn whipped out her key card, "My room number. #191."

Ursula also whips out her key card in response, "Well, you're mistaken because this is mine!"

"Oh my ARCEUS. Please don't tell me you're my roommate." Dawn groaned. "There's no way I'm going to share a room with **_your_** sabotaging ass!"

"We're not roommates, Dawn. Because this is MY room."

"As if I'd just hand it over to you!"

"I got here first!"

"Right, just like how you were also the first to get eliminated from the Wallace Cup, but that's none of my business!" Dawn stuck her tongue out as she played the petty card.

"Bringing up a loss from what was **_years_** ago?" Ursula's irritation became visible in her twitched eyes, "Grow up, Dee Dee!"

"That's because you keep using that age-old nickname from all those same years ago!"

"You're not getting this room!"

"I have a right to be here too, Ursula!"

"Fine! We'll share." Ursula hissed, "You stay out of my way, I stay out of yours."

"Hmph!" Dawn crossed her arms, "And we both get equal halves of this suite."

"Deal." Ursula quickly but reluctantly agrees.

 _I'm probably not even going to be here all that often._ A thought ran through Dawn's head, followed by a mental sigh.

* * *

Over by the docks, three young men had emerged from a small little boat. The one with a Pikachu on his shoulder took a nice, long stretch as the boat sailed off, while the one with the sketch book started a sea portrait. The tallest of them all lowered the map in his hand, knowing for a fact that they'd arrived at Lake Valor's Grand Hotel Resort.

"Alright, Pikachu, we're here!" Ash beamed, pumping his fist up in the air, "Man, we haven't been here since the Wallace Cup. I'm so psyched to be here!"

Tracey finished up the details to his drawing, "Viola, my first Sinnoh Sketch!" he held it up with pride, "This trip is already off to a great start."

Brock stepped forward, eyeing the hotel, "May did say the girls would be here, right Ash? It'd be nice to have the whole gang together again. And it's about time Dawn finally met Tracey."

Before any of them could say a thing, the girls had already been ahead of them. Running towards the docks were Misty, May and Dawn- ready to greet the boys after many years of separation.

"No freakin' way, it's Ash!" Dawn exclaimed as she gave him a hi-five.

"It's so great to see ya, Dawn!" Ash smiled widely, touched that she remembered their signature hi-five after all these years.

"Gosh, Tracey, you barely just got here and you've already finished a full portrait. You just never stop drawing do you?" May giggled.

"Some things never change." Tracey beamed at her.

Misty almost cried when she saw Brock, "I haven't seen you in forever! And what's this about you being a doctor now? Oh my god. I bet you became a doctor just so you can get close to Nurse Joy, huh!" she smirked, arms crossed.

Brock scratched his neck awkwardly, "Well, you see..."

The six chatted it up for a little while, mingling amongst each other. Dawn and Tracey were finally acquainted. Misty and Ash reunited. And May could not wait to explore the Lakeside's mall district with the only guy that didn't dread shopping with her.

She snatched the map from him, pointing at the shopping district, "Brock, you have no idea how many new stores they've put up here! If we go now, we'll have a full six hours to shop before the midnight curfew!"

"Speaking of time," Misty started, "It's about time Ash caught up with the rest of us and actually got himself a car. Everyone else drove here!"

"Misty, do you have any idea how expensive cars are?!" Ash flinched at the amount of zero's that amounted to the price. Pikachu became dizzy at the idea of Ash strapping him to a seat belt, meaning he'd be restrained. (Although Pikachu had a very exaggerated version of seat belt restraint playing in his head.)

"Yeah, but you're the Kanto League Champion now. You could afford it." Misty shrugged.

"Driving takes away all the fun from the adventure!" Ash curled his fingers into his palm, "Plus, uh, I almost backed up mom's car into Gary's house once, so..." he smiled shyly.

"Typical Ash behavior." May beat Misty to the punch as she said that, "But at least someone here finds it charming." she smirked at Misty.

"Don't you dare test me!" Misty chided.

"Huh?" Ash tilted his head, "Who finds me charming?"

Dawn snorted. But after witnessing what Misty almost did to Drew, she knew better than to interfere with matters involving Misty.

" ** _No one._** " Misty said, a little too quickly, "As if any girl would wanna date a guy who doesn't have a car!"

"Guys, I wanna go shopping!" May almost whined, "And I'm also hungry... Brock, let's go!" she tugged on his arm.

"Wait!" Brock stopped her, "What's the rush? We're all here together now, and most of us have traveled with each other before. Don't you think this little reunion calls for a group picture?"

"Oh!" Ash's eyes perked up, digging in his backpack with his hand, "We can take it with my phone. It's the latest model so it's got the best camera!" he pulled out a slim white phone with a pokeball case, installed with the latest Pokedex Updates.

"Whoa, that's so cute!" Dawn exclaimed dreamily, "I'm so getting that model!"

"That's Ash for ya." Misty rolled her eyes, "Always got his priorities messed up, picking a new phone over a car."

"Well, I don't need a car to become the greatest Pokemon Master!" Ash stuck his tongue out at her.

"Uh," Tracey coughs, speaking in a way that only Ash could hear, "However, you do need one if you're planning on taking a certain special someone out on a date."

" **THAT'S RIDICULOUS!** " Ash yelled, his Pikachu shook his head.

Dawn whips out a hairbrush and started carefully brushing through her locks, "So, are we gonna actually do this thing or what? I wanna look as good as I can for our reunion picture! C'mon, it's a pretty big deal."

"Alright, alright!" Brock projects his voice and manages to settle everyone down, getting them ready for the picture.

"Let's take more than one, I wanna send a couple of these to Max back in Hoenn." May smiled and struck a pose.

"Okay... one... two..." Ash beamed for a final click as he raised his phone up in the air to get everyone in the picture, "...Three!" _**Snap.**_

"Pika pi!"


	2. Chapter 2

The girls are all grouped up in suite #192 when the next morning arrives. Drew was waiting outside the door for his scheduled evening lunch with Dawn, under conditions from Ursula that the two would not be meeting alone. Though Drew made it blatantly clear that what they had between them was completely platonic, Dawn wanted to invite May and Misty with them to accommodate for Ursula's insecurities. Which didn't exactly bode too well for Misty.

"Let me get this straight—you want me to joinyou and grass-head for lunch because Ursula's insecure, and that she's not coming because you two can't be in a room together without a fight breaking out?" Misty questioned.

Dawn sighed, "Look, this is the first time we're actually hanging out in real life and May's totally on board with joining us. And she doesn't even have any hard feelings! I just don't want her to be a third wheel around her ex."

Which was true. May didn't seem to display a negative attitude towards him, but she mostly agreed to this because she knew she'd be able to have a conversation with Drew without Ursula's toxic behavior being the subject of what's supposed to be a nice lunch. Plus… Dawn promised to pay, it was free lunch. May _**never**_ turned down free food.

Misty rolled her eyes, "She doesn't have any hard feelings because she knows you're gonna feed her! Why else would she ever be in the same vicinity as that fuckboy of an ex?"

It didn't take long for Dawn to find out that _**fuckboy**_ was the term Misty constantly used to refer to Drew, because she absolutely refused to use his name. And if it wasn't fuckboy, it was grass-head. Dawn had no idea where she came up with these things.

"Do you want me to treat you as well?" Dawn asked with an innocent smile.

"That's not the point!" Misty yelled, "What makes you think he and I would get along any better than you and Ursula? I'm not trying to get kicked out of The Seven Star Restaurant just because you wanted to dine with the devil!" she turned away, crossing her arms.

"I-I wouldn't say he's the devil…" May interjected.

"Oh, wake up already, May!" Misty threw her arms up, "We're barely two days into the best trip ever and you've already gotten feelings for him again, haven't you?"

"I didn't even get a chance to talk to him properly!" May shouted back, "Look, Dawn's not the only one here that wants to catch up with a friend face to face, okay? You guys promised to be civil."

"Me staying behind would be much more civil." Misty retorted.

"Well, if that's how you feel. I guess I can't force you to come with us," May sighs, and whips out her phone to shoot a text, "I wonder of Ash is free right now…"

Misty's eyes perked up at the sound of his name right away, "He'll probably decline. I'm sure somewhere in that thick skull of his, he'd have enough common sense to deny bad company."

May's phone makes a _**ping**_ sound. It was a reply from Ash.

"Oh look, Dawnie!" May passes her phone to Dawn, "He happily accepted the invitation, do you mind if he comes?"

"Nope, not at all," Dawn shook her head and beamed at her, "I guess we can get going, then!"

"W-What?!" Misty exclaims out of surprise, "Ketchum can't possibly be that stupid!"

"Misty, if you're not joining us, then you don't have anything to worry about." Dawn shrugged.

Misty huffed, scrambling her mind for an excuse, "You know what? I'm going, too! Can't have grass-head spreading his fuckboyatry onto Ash. I've gotta be there to prevent that!"

May and Dawn shook their heads in unison. They would've saved so much time if they'd just mention Ash in the first place.

The three of them were met by Ash and Drew as soon as they opened the door. May locked down their suite, while Dawn explained to Drew that the lunch arrangements have been adjusted due to the addition of Ash and Misty.

"Huh?" Ash tilted his head, confused, "May told me that Misty didn't even wanna come, so that's why I got invited."

Misty quickly whirled around, "T-The more the merrier, you know?" she started laughing nervously.

"Uh… okay, I guess." Ash scratched the back of his head, the puzzled expression on his face doesn't seem to falter. Even Pikachu couldn't seem to figure it out.

* * *

The group headed over to their table of six, claiming their seats.

"Wow!" May's eyes started to gleam at the menu, "They've made so many additions since the Wallace Cup. I don't know what should I eat first!"

Drew sat across May, chuckling at the look on her face as he went over the selections on the menu. _It seems like some things don't change,_ he mused.

Misty settled herself next to May, at the very end of the table and faced Ash, "Well, this is my first time here. So, what would you recommend, Ash?"

"Oh man," Ash replied, "Where do I start?" he shared his menu with her, enthusiastically pointing at all of the items. His Pikachu joined in on their sparked-up conversation.

Dawn was placed on the other end of the table, with an empty seat in front of her. It'd hit her just now that she became the fifth wheel, but didn't necessarily bother her. She started flipping through the pages on her menu, listening in on the others interacting with each other.

The five of them lifted their heads up in shock at the sight of their waiter.

"So, what can I get for you?" The waiter pulls out a small note pad and flashes a smile.

"Gary?!" Ash blurted out, "What are you doing here?"

"I used to wait tables here before I became a big name in Pokemon Research," Gary shrugged, "so naturally, they called for me when their restaurant was low on staff."

"Huh, so my roommate is the waiter," Drew nodded, "that explains why you woke up so early."

May gasped, "Gary Oak is your roommate?"

Misty grumbled to herself, "Of all the restaurants in Sinnoh…"

"What will the lady be having today?" Gary winked at May. He took notice of Dawn's head buried in the menu, feeling almost ecstatic to know she was here.

May opened her mouth to explain that she wasn't ready to order yet, only to be stopped by Drew.

"Don't worry, May. I'll order for you," Drew passed a piece of paper to the waiter, "The lady will have that."

"Uh, okay-" May looked over at Misty in confusion.

Misty murmured, rolling her eyes, "He's just buttering you up."

"Well, I think it's sweet!" Dawn chimed in, handing their menus back to Gary as soon as all of their orders were taken, "And I'll make sure you get a very nice tip." She said to him quietly.

"Nice try, Dawn," Gary laughed, "but I won rock, paper, scissors yesterday. You can't tip your way out this."

"No need to worry," Dawn said, "I promise I'll make time to tell you about all my adventures! But you need to do your job right now."

"I'll hold you to that." Gary pointed to her as he headed backwards into the kitchen.

Ash leaned in towards Drew and whispered, "Hey, why's Misty looking at you all scary like that? Did you do manage to do something to piss her off, or what?"

Drew twitched for a mere second, "I think _**she**_ could explain that better. Could you, Misty?"

Misty smiled at him, "I don't know what Ash is talking about. I'm being completely civil here, just like I promised May. Even though you hurt her real-"

"So, Drew!" May exclaimed in an attempt to drown out Misty's jab at him, "How have you been ever since you became a Top Coordinator? You must have more fans than _**ever.**_ I mean, you had a lot of fans before, I can't imagine the amount you must have now. We should share our coordinating experiences together!"

Ash placed his palm on his head, trying to make sense of all of this, "But why would Drew hurt May? Doesn't he really love h-"

"Ash!" Dawn shouted, "Don't you know it's rude to interrupt? You should be holding a nice conversation with Misty, instead! I'm sure she'd really appreciate that."

"But Dawn," Ash frowned, "Didn't you interrupt me just now?"

"She's right," Misty sighed loudly and faced him again, she had no choice but to play along, "You know, I've been thinking about you a lot lately." She started off, almost regretting her words.

"Huh? Really?" Ash smiled, "That makes me so happy to hear!"

Dawn let out a relaxed sigh and slid her back into her chair as the two pairs managed to get lost in their own conversations. This was why she wished she was traveling with Brock again, because he always knew how to settle them down. Just as the thought ran through her head, she recognized the soft flash of purple matched with a poker face walking by their table. _Paul._

She hadn't seen him in _**years.**_ Last Dawn heard, he'd become the Sinnoh League Champion right around the same time both her and May became Top Coordinators. Paul was in a couple of interviews at the time, appearing to have somewhat changed in behavior overtime.

He looked at her with what seemed like indifference, and kept walking.

"Um," Dawn uttered nervously, knowing this could only end badly, but choose to not care anyways, "Hey, Paul. There's an empty seat left, would you like to sit with us?"

The whole group stopped talking as soon as they heard his name. Everyone knew the infamous Champion Paul. May and Misty had the full scoop of how horrible he used to be towards Pokemon from Dawn, Ash, and Brock.

"Dawn, what do you think you're doing?" Misty said in a hushed tone.

"Isn't that the really rude trainer whose awful towards people and Pokemon?" May asked rather loudly, her words had no tact.

"C'mon, guys. Relax," Ash reassured them, "It's okay."

Paul stopped in his tracks and turned to face her. He appeared surprised at her invitation.

"I could share my food with you, if you want." She offered.

He ushered over to the group, not responding to a single thing she just said, before finally sitting down and facing her. "I won't eat off your plate, but I don't mind joining you for a bit before training again. It's Dawn, right?"

"Wow, you actually remembered my name!" Dawn beamed widely at him, and turned to Ash, "Thank you."

"No problem!" Ash grinned, giving her some thumbs up, "And congrats on becoming the Sinnoh Champion, Paul!"

"Thanks," Paul managed to say, "Congrats to you on the Kanto League."

Gary returns back with Drew and May's food being the first to arrive, and eyes at the new company that joined them. The plum haired boy sitting in front of Dawn extremely hard to miss.

When May lifts up the silver plate cover off of her dish, she immediately recognized its contents. Red pokeblocks chopped up on the side of yakitori and omelet rice, drenched with cheri berry sauce.

"You remembered?" she glanced over at Drew, who was already slicing his steak with a knife.

He offered her a smile, "How could I forget? It was your favorite dish back in Johto."

May almost flushes, her lips curved back at him.

Misty eyed May's food rather strangely, "Wow, May. That's an awfully… red dish, you should get straight to eating it before Pikachu does." she smirked at Ash, his Pikachu scratched its head in embarrassment.

"Nah, Pikachu knows better than to eat May's food. After all, we _**have**_ traveled with her before!" Ash chuckled, his eyes starting to shine as soon as Gary places his dish in front of him, "Oh, boy. I can't wait to chow down on this!"

Gary gets to Dawn last.

"Here you go," Gary says, placing the food in front of her, "can I get you anything, sir?" he asks, studying him. Ash, Dawn, and Brock all gave Gary and earful about this one. So why would Dawn even let him into their group?

Paul shook his head, not even looking up to see who the waiter was.

"You sure you don't want anything, Paul?" Dawn offers again, "I don't want you to feel left out."

"I guess I'll have a glass of water," Paul shrugged, "and I'm sure it's not me who feels left out."

"Water. Got it." Gary gave Dawn one last look before heading off to the kitchen again.

Dawn smiles at Gary and waits until he's out of sight, "What do you mean?" she shook her head, not yet lifting the lid off her food.

"You invited me over here because you're the fifth wheel, am I correct?" he states rather bluntly, "Red-head's with Ketchum, your traveling companion is with that other famous coordinator, and you're with no one." His last words were like a pinch on the neck.

"I asked you to come over because I haven't seen you in so long," she replies, "Well, if you count the media, that is. But, really! I genuinely wanted to talk to you. I don't really care about stuff like dates. I just wanna have fun with my friends!"

Paul shrugs again, "It's not like I care. I will admit, though. You do surprise me, troublesome. You'd consider me a friend after how I acted towards you and Ash."

"You ended your last battle with Ash on good terms," Dawn began, lifting the lid off her dish, pushing it closer to Paul, "all is forgiven."

The astonishment on his face is hard to miss, "Thank you…" he mumbles.

Everyone in the group started to share stories and old memories with each other, May started off by telling the story of how Dawn became her traveling companion. Ash caught Misty and the others up to speed on his Kanto championship, while Dawn kept poking fun Drew for the username name he used on pokepen. Paul shared his new battling strategies with Ash, and Drew got Dawn back by making fun of the fact that her username name came from her usual catch phrase.

"No need to worry!" Drew mocked Dawn in a high-pitched tone.

"Aw, man. You should see Dawn do impressions of other people, Drew. They're hilarious!" Ash exclaimed.

"Er hem," Dawn coughed, and lowered her voice octave, "I like Roserades because they have _**so**_ much more elegance than the average human being. Which makes them the superior Pokémon!"

Drew laughed, "Am I wrong, though?"

Before anyone could retort, their little banter was interrupted by a voice that didn't belong to any of the six at the table.

"Oh, my gosh! Is Dane Berlitz and Paul on a _**triple**_ _**date**_?!" the voice booms through the corner of the room, coming from a brunette wearing a mushroom hat, who was skipping over to their table.

"L-Lyra!" Dawn spat, already reeling from the awful familiarity of Lyra's matchmaking, "Okay, so I gave him a peace offering. We're not even _**that**_ close!"

"Ugh," Lyra rolled her eyes, "and here I was, rooting for you and Ash the entire time. Tsk tsk tsk, Dane."

Misty stabbed her food with the knife, glaring at the two, "Excuse me, Dawn and _**Ash**_?!"

Dawn shook her head rapidly, "It's not like that, I swear! Not once during our journey did I _**ever**_ think of Ash that way. I don't even care about boys!"

"Gee, Dawn, is there another way you could've put that?" Ash grumbled jokingly.

May cleared her throat to speak up, "Oh, um, we're not on a date."

"Which was what I was trying to tell her." Dawn gave Lyra a disapproving look.

Lyra giggled and whispered to Dawn, "This is the perfect opportunity for me to work my magic."

"Um, Dawn. Who is this girl?" Misty looked at Lyra questionably.

"That's one of the friends we've met during our travels. Johto League Champion, Lyra," Ash spoke up instead, "she has a thing for playing cupid for other people."

"Wait a minute!" May clapped her hands together enthusiastically, "Drew, we've met her before! She has a matchmaking service in Johto."

"The hat is kind of hard to miss." Drew retorts, taking a bite of his food.

"That's right!" Lyra exclaims, "But all cupid business aside," she walks over to May and Drew, "You two had a history, didn't you?"

Dawn huffed out a huge sigh, just now realizing what she meant when she said she'd work her so called _**magic**_ , which Dawn already tried, "Lyra, that is not your place to pry!"

"Well, yeah," Drew kept his composure anyway, despite his discomfort, "but now I have a girlfriend."

Lyra notices the way May flinches ever so slightly at the word _**girlfriend**_ and curves her lips into a small smirk, "While it is very unfortunate that such a _**perfect**_ pair have split apart, at least the two of you have moved on and are now dating other people."

 _This could not be good,_ Dawn rubbed her temples.

Misty widened her eyes in anticipation, sharing the same thought as Dawn.

"Wait," Drew stopped and looked directly at May, "You're seeing someone?"

May attempted to speak up only to be talked over by Lyra, who exclaimed, "Don't be ashamed to admit it, May! I know you've kept it pretty low for a while but it's about time you finally went public about your new boyfriend, _**Gary Oak**_."

Ash spat out his tea, "What?!"

Misty face-palmed, "It's just fuckboy after fuckboy with you. Is it, May?!" she glared at Lyra, "That's the worst boy you could lie-"

"You're… going out with my roommate?" Drew said this slowly, "Gary did say there was a coordinator he hoped to see while he was here… said that she was pretty famous, too. I just didn't know that it was you, May."

"And here's your water, sir." Gary came back with a glass on a tray and set it down, then looked at everyone else that was staring at him, more so Drew, "Uh, can I help you guys with something?"

Paul chugged his water and stood up from his seat, walking away.

"Hey, Paul," Ash whipped his head around, "Where're you going?"

"I'm leaving this circus show," Paul stated harshly, "It's getting a little too crowded for me. Later."

Gary frowned at Dawn, "It was very rude of him to leave like that."

She shook her head and beamed at him, "It's just the way he is. Besides, I'm not too worried about him anyways."

Drew slid his chair from the table and stood up hastily, "I'm gonna head to the restroom."

"If you say so, Dawn," Gary then left the table with the bill as soon as Drew left.

The remainder of the group was briefly silent.

Lyra winked at May and wagged her finger, "Thanks to me, you've one upped Drew by dating Gary. Who's a huge upgrade in comparison to Ursula!"

May took a deep breath and proceeded to speak calmly, "Except for one little thing…" she banged her fist on the table, " _ **I'm not actually dating Gary Oak. I haven't even properly met him!**_ "

Misty turned to Dawn, "So, what are you gonna do about this, Dawn? Lyra is _**your**_ friend."

"Me?!" Dawn exclaimed, "It's Lyra who lied. I had nothing to do with this!"

Ash and Pikachu looked up to where Lyra stood earlier, only to find that she'd just disappeared.

"Uh, guys…" Ash began, "Lyra's gone."

"Oh, great!" May groaned, "Now when Drew finds out, he's gonna think I made it all up just to make him jealous!"

"I think that was what Lyra was aiming for," Misty pointed out, "she's "cupid" remember?"

"Well, cupid's going to make me look stupid as soon as Drew realizes that Gary barely even knows who I am!" May's voice rose with panic.

Dawn breathed in, "Alright, listen up!"

Everyone turned their attention to her.

"I know exactly who can help fix this," Dawn announced, huddling the group together, "after Drew comes back…"

After Dawn explains the plan, the bill was paid with a generous tip left behind. Drew lingered at the table for a bit, taking a look at the bill book. Inside was two hundred dollars and a note written on a napkin.

 _This if for you being such a good waiter._

 _Oh, and I'll make sure I uphold that promise._

 _Let me know when you're free!_

 _I'll be waiting._

 _XOXO_

 _(P.S) You look really good in that vest._

Drew felt a presence and stuffed the note back in the book.

"Hey, Drew," Gary beamed, "can I do something for you?"

"Actually, yeah, you could." Drew breathed in, "take care of her, okay? You're a really lucky guy." He turned his back onto Gary and caught up with the rest of the group.

"What was that all about?" Gary stood there dumbstruck, "Ah, well." He shrugged, picking up the bill.

* * *

Drew went back inside his suite that night while everyone else grouped up in suite #274 which belonged to Tracey. The adults were usually a couple of stories above the minors, so it took a bit of an elevator trip up. Misty, May, Dawn and Ash were all seated on the living room couch of the room. Adult suites felt much more spacious, since they didn't have to have a roommate. Tracey took the courtesy of filling the empty walls up with paintings.

"Are you guys sure about this?" Ash asked, not feeling too good about the situation, "I just kind of feel like we could fix this problem by being honest."

"Honest?" May snapped, "You clearly don't know Drew at all! He'd tease me endlessly about a failed plan to make him jealous and rub it in my face that he'd been the one to move on before I did! I'd just look desperate if I came clean."

 _Clearly, it seems that you don't know Drew either._ Dawn thought. He seemed like a really nice and understanding guys in those letters and messages. It was hard to imagine him ridiculing her like that. But then again, maybe it was Dawn that didn't know him well. After all, they'd only been friends for over a year through letters and emails. May had a lot more history with him than that.

Tracey put his paint brush back on his easel and moved over to sit on the couch, "So, what's this all about?"

Brock was the last to show up, "Dawn sent me a text saying it was an emergency." he huffed, drained of all the energy it took to run from his room to here.

Ash shrugged nonchalantly and eyed at Dawn.

Misty was ruffling Pikachu's fur.

May shook on the couch in panic.

Dawn took a deep breath, "Lyra told a really big lie and we need your help to fix it."


End file.
